Benzyl resorcinols



Patented Feb. 7, 1928.

UNITED sTATEs PATENT OFFICE.

ALFRED R. L. DOHME, OF BALTIMORE, MARYLAND, ASSIGNOR TO SHARP do DOHME,

INC., 0F BALTIMORE, MARYLAND,

A. CORPORATION OF NEW JERSEY.

BEHZYL nnsoacmons.

No Drawing.

This invention relates to a new chemical The new compound is obtainablefrom resorcinol by the action of benzoic with the presence of acondensing agent, such as zinc chloride, with resulting production of anintermediate ketone, benzoyl resorcinol, which is then subjected toreduction to produce therefrom the benzyl resorcinol.

The invention will be further illustrated by the following specificexample. The parts are by weight i There is heated together in an openvessel 50 parts of resorcinol, 75 parts of benzoic acid and*75 parts ofzinc chloride until the reaction begins. The source of heat is removedand the reaction allowed to continue until it ceases. Upon addin waterthere" separates out a reddish yel ow oily substancewhich is benzoylresorcinol, a ketone of the formula C H (OH),.COG,H and some unactedupon benzoic acid. To this mixture is added enough sodium carbonate todissolve both the ketone and the benzoic acid. Carbonic acid gas is thenpassed thru this mixture when the ketone is thrown out of solution as anoil and can be separated.

readily from the aqueous solution. It is purified by recrystallizationfrom benzolwhen it appears in the form of white. crystals with meltingpoint 142.143'degrees G. The new ketone so'produced is then mixed in avessel supplied with a reflux condenser with zinc amalgam and dilutehydrochloric acid in the proportion of parts of ketone, 200 parts ofzinc amalgam and 600 parts of dilute hydrochloric acid and boiled for 10hours or more. As a result a pale yellow to colorless oil separates outof the aqueous liquid. This "is separated, redistilled in vacuo andrecrystallized from benzol when it separates out in white crystals.

The product thus produced is the new substance benzyl-resorcinol theformula, product in a pure state forming white crys- Application. 111...October 9, 1923. Serial no. seam.

method (U. S. Hygienic Laboratory modifi cation). It is, nontoxic andpossesses valuable therapeutic properties, among which may be mentionedthose of a germicide and antiseptic.

I claim; l. The method of making benzyl resorcinol which comprisessubjecting purified benzoyl resorcinol tothe action of zinc amalgain andhydrochloric acid and subjecting the resultin impure benzolxresorcinolto a vacuum distillation followed by a recrystallization from benzol; 2.The method of making benzyl resorcinol which comprises subjectingpurified benzo l resorcinol to reduction.

3. he method of producing benzyl resorcinol which'comprises subjectingbenzoyl resorcinol to the action of zinc amalgam and hydrochloric acidand subjecting the resulting impure be '1 resorcinol to vacuumdistillation followe by'recrystallization'frombenzol. 4. Asa new roduct,benzyl resorcinol of ,H, (OH) CHALK said tals, melting point 7879 C. andhaving valuable-therapeutic properties.

a 5. Process of manufacturing benzyl resorcinol, consisting of boilingtogether benzoyl resorcinol, amalgamated zinc and dilute hydrochloricacid.

In testimony whereof I aifix m .si ature.

ALFRED R. L. 0%.

